Acetonitrile → HCID 59452068, compound

HRID 1891204Notes

Reaction equation

HRID 1891204 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[C:15](=[O:18])([O-])[O-:16].[Na+].[Na+].[C:21](#[N:23])[CH3:22]>>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:8]2[CH2:22][CH2:21][N:23]([C:15]([O:16][C:6]([CH3:11])([CH3:7])[CH3:4])=[O:18])[CH2:10][CH:9]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 59452068HCID 59452068, compound

Conditions

Temperature
70 °C

Procedure

To a flask containing a portion of the enol triflate prepared above (8.00 g, 24.2 mmol) were added 4-ethoxycarbonylphenylboronic acid (6.09 g, 31.4 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (1.693 g, 2.42 mmol). Acetonitrile (100 mL) and sodium carbonate (60 mL, 1.0 M aqueous, 60.0 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 18 h, then was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 10% EtOAc in hexanes, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 231.9 [M-Boc]+; 1H NMR (500 MHz, CDCl3) δ 8.00 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 6.20-6.10 (m, 1H), 4.37 (q, J=7.0 Hz, 2H), 4.10 (br m, 2H), 3.66-3.64 (m, 2H), 2.54 (br m, 2H), 1.50 (s, 9H), 1.40 (t, J=7.0 Hz, 3H).

Workup

  1. customprepared above (8.00 g, 24.2 mmol)
  2. customthe resulting mixture was degassed via nitrogen
  3. customsparge
  4. temperatureto cool to ambient temperature
  5. additionwas poured into water
  6. extractionThe mixture was extracted with EtOAc
  7. concentrationthe organic phase was concentrated in vacuo
  8. customPurification by chromatography on silica gel (0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-45516ac1fe9e46cfb8b1ef667f4b1bf5
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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